ArticleJournal of the American Chemical Society2018
Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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23 citing papers in PubMed, 61 citations in OpenAlex.
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- Genetically-modified activation strategy facilitates the discovery of sesquiterpene-derived metabolites fromSynthetic and systems biotechnology · 2025Article
- d-Galactose-Esterification of a Fungal Polyketide Catalyzed by a Carnitine Acyltransferase Domain.Chembiochem : a European journal of chemical biology · 2025Article
- Exploring the Nonenzymatic Origin of Duclauxin-like Natural Products.Journal of natural products · 2024Article
- Convergent approach for direct cross-coupling enabled by flash irreversible generation of cationic and anionic species.Nature communications · 2024Article
- Enzymatic Benzofuranoindoline Formation in the Biosynthesis of the Strained Bridgehead Bicyclic Dipeptide (+)-Azonazine A.Angewandte Chemie (International ed. in English) · 2023Article
- Genome Mining and Screening for Secondary Metabolite Production in the Endophytic FungusMicroorganisms · 2023Article
- Deciphering chemical logic of fungal natural product biosynthesis through heterologous expression and genome mining.Natural product reports · 2023Review
- Late-stage cascade of oxidation reactions during the biosynthesis of oxalicine B inActa pharmaceutica Sinica. B · 2023Article
- Mining and characterization of the PKS-NRPS hybrid for epicoccamide A: a mannosylated tetramate derivative from Epicoccum sp. CPCC 400996.Microbial cell factories · 2022Article
- Chimeric natural products derived from medermycin and the nature-inspired construction of their polycyclic skeletons.Nature communications · 2022Article
- Discovery and characterization of a terpene biosynthetic pathway featuring a norbornene-forming Diels-Alderase.Nature communications · 2022Article
- High Diversity of Type I Polyketide Genes inJournal of fungi (Basel, Switzerland) · 2022Article
- A validated high-throughput method for assaying rat lungworm (Parasitology · 2022Article
- Cloning and Functional Characterization of the Polyketide Synthases Based on Genome Mining ofFrontiers in microbiology · 2022Article
- De novo biosynthesis and gram-level production of m-cresol in Aspergillus nidulans.Applied microbiology and biotechnology · 2021Article
- Structural Basis for Selective Oxidation of Phosphorylated Ethylphenols by Cytochrome P450 Monooxygenase CreJ.Applied and environmental microbiology · 2021Article
- Duclauxin Derivatives From Fungi and Their Biological Activities.Frontiers in microbiology · 2021Review
- Bioactivity Potential of Marine Natural Products from Scleractinia-Associated Microbes and In Silico Anti-SARS-COV-2 Evaluation.Marine drugs · 2020Review
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8 authors at 2 institutions in 2 countries.
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Abstract
Duclauxins are dimeric and heptacyclic fungal polyketides with notable bioactivities. We characterized the cascade of redox transformations in the biosynthetic pathway of duclauxin from Talaromyces stipitatus. The redox reaction sequence is initiated by a cupin family dioxygenase DuxM that performs an oxidative cleavage of the peri-fused tricyclic phenalenone and affords a transient hemiketal-oxaphenalenone intermediate. Additional redox enzymes then morph the oxaphenoalenone into either an anhydride or a dihydrocoumarin-containing monomeric building block that is found in dimeric duxlauxins. Oxidative coupling between the monomers to form the initial C-C bond was shown to be catalyzed by a P450 monooxygenase, although the enzyme responsible for the second C-C bond formation was not found in the pathway. Collectively, the number and variety of redox enzymes used in the duclauxin pathway showcase Nature's strategy to generate structural complexity during natural product biosynthesis.
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